This post covers the best things to do in Chicago this January, including, free, family-friendly, as well as nighttime activities, all updated for 2020.
- Top 10
- Nighttime Activities
- Free Things to Do
- Things to Do (Any Time of Year)
- How’s the Weather?
TOP 10 EVENTS AND THINGS TO DO IN CHICAGO IN JANUARY
January in Chicago is a great time to experience because it is a slow season for tourism which means you won’t have to wait in lines or stand in crowds!
For some of the more popular things to do in Chicago, read the following posts:
1) Go to a Sporting Event
There is nothing more Chicago than cheering on our sports teams!
In January, you can head west to the United Center for a basketball or hockey game.
For a list of all sporting events happening this month, check this list.
Click here to find all sporting events happening this month.
2) Go to a Concert
January is the perfect month to stay inside and enjoy a concert during the cold evenings.
Here are just a few of the larger-scale concerts happening in January of 2020.
For a list of all concerts happening this month, check here.
- Disco Biscuits - January 2-4 at the Riviera
- Surfaces - January 10 at the Metro
- Tedeschi Trucks Band - January 17-18, 24-25 at the Chicago Theatre
- Chris Lane - January 17-18 at Rosemont
- Ben Gibbard - January 24-25 at Thalia Hall
- Lauren Alaina - January 24 at Rosemont
- Cold War Kids - January 25 at the Riviera
- Rex Orange County - January 27 at the Aragon Ballroom
- The Rat Pack is Back - January 31 at Rosemont
You can find all the concerts happening this month here.
3) Go on a Sightseeing Tour
Put on your parka and be sure to layer for our January tours! Join our history-loving Chicago-adoring tour guides on foot.
We offer pay-what-you-like walking tours every day of the week in the Windy City.
If you’d prefer to enjoy a bus tour, we have a great comparison of Chicago’s best. From hop-on-hop-off buses to dedicated tours, you’ll find one to suit you here.
4) Go to the Theater
Chicago is home to many many regional theatres, small black box spaces, and Broadway Tour houses. There is something for everyone!
To see all the theatre productions happening this month, look here.
Here are just a few of the many shows happening in January 2020.
- Blue Man Group runs continuously and is a great show for everyone in the family. They are famous for their funny mimed skits that incorporate dance, music, and electronic visuals.
- Hamilton at the CIBC Theatre runs until January 5, 2020. This is the story of Alexander Hamilton- performed with music and rap!
- Phantom of the Opera, a theatre classic, runs December 2019 - January 5, 2020.
- Mean Girls is a fun, new musical adaptation of the movie that runs from December 25, 2019, to January 26, 2019.
- Once on This Island that runs from January 21, 2020, to February 2, 2020, will help you imagine feeling warmer during the cold winter!
Check here to see a full calendar of all shows and get a real taste of Chicago theatre.
Pro-tip: Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the downtown Loop.
5) See More for Less with a Chicago City Pass
Many of Chicago’s biggest attractions have entry fees.
While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.
They can also save you time with skip-the-ticket-line privileges.
Each Chicago tourist discount pass includes a variety of fun activities and attractions.
Here are a few examples of what you can visit with a tourist pass, for a discount or for free.
- Shedd Aquarium
- Skydeck Chicago
- Adler Planetarium
- Art Institute of Chicago
- The Field Museum
- Museum of Science and Industry
- 360 Chicago Observation Deck
For more details, make sure to read our full post covering Chicago tourist passes.
6) Sketch Comedy Festival
Perfect for the Comedy Capital of the world, this festive highlights over 1,000 performers in the 180+ shows that take place during these 10 days.
Founded in 2002 with just 35 local performers, Sketch Comedy Fest has now become the largest of its kind in the world, drawing in writers and performers from across the globe.
7) Ice Skating in Downtown Chicago
Ice Skating is a great way to spend the day or evening hours, especially with numerous rinks around the city.
There is the McCormick Tribune Ice Rink in Millennium Park.
Right underneath Cloud Gate and on the edge of the downtown area makes this a perfect spot, and you can warm up with some hot chocolate served right next to the rink.
Across the bridge in Maggie Daley Park, you will find the Skating Ribbon.
Surrounding the rock wall and with the skyline in the background, this is experience aims to give you the feeling of skating through the alpines.
For both rinks, skating is free and rentals are $12 on weekdays, $14 on weekends.
8) Take a Tour of a Local Brewery
Are you in Chicago and looking where to find a good local pint? Chicago is a great city to enjoy a local microbrew in one of our fantastic neighborhoods.
Many restaurants have enough space to brew their own beer like Berghoff’s, Gino’s East, and Rock Bottom, but if you want to try multiple Chicago Brews, these bars are great.
Everyone has their favorite places for a pint, of course.
Click here for Chicago Brewery Tours!
9) Indulge in Chicago Food
Explore Chicago’s delicious food! Head to a popular Chicago restaurant like Girl and the Goat to try Chef Stephanie Izzard’s amazing dishes.
Looking for a sweet treat? Try Stan’s Donuts with locally roasted coffee!
If you are looking for something more casual - try a Chicago Hot dog or an Italian Beef sandwich!
10) Tomorrow Never Knows Music Festival
For a decade, people have been braving the January weather for this music festival.
Tomorrow Never Knows celebrates up-and-coming local indie artists, as well as draws in national acts, musicians and comedians alike.
Hosted in different independent venues across this city, this provides a true Chicago experience.
The festival runs from January 15 - 19, 2020.
THINGS TO DO AT NIGHT IN JANUARY
Chicago offers many free activities throughout the year. Here are a few suggestions during January 2020.
Be sure to read our post about the top things to do in Chicago at night for even more suggestions.
Adler After Dark
On the third Thursday of each month, Adler Planetarium opens up for a fun night-time event for adults.
There will be drinks, music, and entertainment while enjoying looking at the stars. Escape the cold and enjoy this monthly event.
Check out a Drag Show
Head to the South Loop to attend Lips Drag show which has been around for 25 years.
It has performances Wednesday - Sunday; including a Sunday brunch!
MSI After Dark
The MSI After Hours is an Adults Only experience to explore the museum after the day time guests have left.
Each After Hours event lets you enjoy cocktails, beer, snacks, and new programs each month.
See the Local Music Scene
Check out the local music scene in Chicago, take a look at some of the more popular venues:
Go Out for a Cocktail
Chicago has more speakeasies – fitting for the mobster history of the Windy City.
If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.
Go to a Game Bar
Explore some of Chicago’s best game bars. Whether you want to try an arcade bar with some pinball and Packman or try a classic board game, Chicago has a bar for you.
Check out our favorite game bars across the city.
Be sure to check out our post on top things to do in Chicago at night for even more suggestions.
FREE THINGS TO DO IN JANUARY
This section lists more free events, activities, and attractions so see in Chicago this month.
For more ideas, check out our post about the Top Free Things to Do in Chicago.
Maxwell Street Market
Bundle up to enjoy the international flare at this market on Sunday mornings between 7:00 am - 3:00 pm which has been a Chicago tradition for over 100 years.
Take in the bargains and culture at this year-round market.
The market has free admission. For more details, click here.
Take yourself out on a Self-Guided Food Tour
If you want to experience Chicago through your taste buds, try one of our self-guided food tours. Head to Chinatown to explore and enjoy savory buns and Peking duck.
Pilsen is a wonderful neighborhood where you can appreciate the rich Mexican culture of the area while enjoying tasty dishes.
Small but might Little Italy is definitely a neat neighborhood to experience too! Get out of downtown to the northside neighborhood Andersonville for a little shopping and tasty bites in the Swedish neighborhood.
The Watertower Museum
Go into the bottom of the Watertower for a small but mighty free art museum!
If you are joining us on our Pay-What-You-Like Magnificent Mile walking tour- you will enter this museum with your tour guide.
Art on the Mart
Most nights in January Art on the Mart will be in full swing!
Head the Riverwalk at sunset to see an amazing art projection on the Merchandise Mart Building - a building so large, it has its own zip code!
The Bridgeport Art Center
Located in the Bridgeport building which is a creative home for local artists and designers, there is an outdoor sculpture garden and three curated art galleries.
On the 3rd Friday of each month between 7:00 pm - 10:00 pm, people are invited to see the painters, sculptors, photographers work.
Check out the Chicago Cultural Center
A great place to warm up while appreciating architecture is the Cultural Center. This beautiful and historic building is free and open for the public to explore.
Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here.
This is also a great place for children’s programming.
Check out their calendar of events to see what is going on during your visit.
There are many Chicago museums that are free! Check out our free museum list here.
Also, if you happen to be a local traveler - be sure to check for free museum days during the winter months in Chicago.
For even more free activities, see our post on the top free things to do in Chicago.
FAMILY-FRIENDLY THINGS TO DO IN JANUARY
Below we list several great options to keep your children entertained this month, including parks, museums, and theater!
Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.
Winter WonderFest (November 30-January 6)
Navy Pier’s Festival Hall transforms into an indoor holiday theme park called Winter WonderFest, with music, skating, carnival rides, and entertainment.
Children shorter than 3 feet tall are free.
This is a great event for families with little kiddos and runs through January 6!
Northerly Island Adventure
Head to Northerly Island to explore with the kids during some official free exploring days.
See birds of prey and wolves, make nature-inspired winter crafts, walk on snowshoes and drink cocoa at Polar Adventure Days on January 26, 2020.
This event is free to attend.
See Corduroy the Play
See the play Corduroy, which runs November 15 - January 5, 2020, at the Broadway Playhouse performed by the Emerald City Theatre company.
This is an excellent story for the whole family adapted from the children's books about a.
Light Show in the Garden
Head a stretch North to the Chicago Botanic Garden to see the new event Lightscape. The garden is transformed into a twinkly wonderland.
You walk on a one-mile path that includes majestic trees, water features, and stand-alone lighting installments.
The light show is active from November 22, 2019 - January 5, 2020.
See Trolls Live at the Chicago Theatre
Sit in the iconic Chicago Theatre with the kids and watch Trolls Live! There are three performances per day.
- Dates: January 11 - 12, 2020
- Times: 10:30 am, 2:00 pm, 5:30 pm
- Prices: From $53+
Find tickets for Trolls Live! here.
Juice Box Concerts at the Cultural Center
Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am - 11:45 am for an engaging musical event!
While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6.
Go to a Museum
January is a great month to have a few indoor options for the family in Chicago so bringing the youngsters to an indoor museum is always a good idea!
Chicago has a lot of museums that are very interactive and ideal for kids such as:
- Where to Store Your Luggage
- Tourist Attraction Discount Passes
- Chicago Bus Tours
- Chicago Walking Tours